6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → (RS)-6-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butylamino]-4H-benzo[1,4]thiazin-3-one

HRID 1801470Notes

Reaction equation

HRID 1801470 reaction equation
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]2[S:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=2[CH:25]=1>CCO.O>[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][NH:14][C:15]1[CH:16]=[CH:17][C:18]2[S:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=2[CH:25]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

Product 1

HCID 67222623(RS)-6-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butylamino]-4H-benzo[1,4]thiazin-3-oneYield 29%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of (RS)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (4 g, 20 mmol; prepared according to Heterocycles (1987), 25(1), 329-32) and 6-amino-4H-benzo[1,4]thiazin-3-one (4 g, 20 mmol) in EtOH/water 9:1 (140 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4) to afford the title intermediate as a brown oil (2.2 g, 29% yield).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4)

Sources & evidence

ORD record
ord-1cd0fcbdc1494d50a83cf1f581fe9830
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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